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Valentine’s Day in Portland: 5 Awesome Outdoor Outings

Originally written for RootsRated

Sure, you could make reservations at a fancy restaurant for Valentine’s Day, and along with it, drop tons of cash and deal with crowds for what will more than likely be an overpriced meal. But with that all-important holiday fast approaching, any creative Portlander would do well to think outside the box (or, rather, outside the bar) when it comes to a memorable, adventurous date. And with easy access to innumerable outdoor excursions, there are plenty of exciting, adventurous ways to spend the holiday, whether with that special someone or on your own.

Romantic hikes, tandem bike rides, muddy runs, and solo sojourns are just a few options for making the most of a memorable Valentine’s Day in Portland. Here, some sweet ideas.

For a Romantic Hike

Multnomah Falls makes for a majestic outing no matter which viewpoint you choose. Szapucki, mods made


What’s not to love about the Wahkeena Falls-to-Multnomah Falls Loop? The hike offers one of the best waterfall views in the state, a secluded forest, and a stop at the Multnomah Falls Lodge (which serves tasty treats for hungry hikers). Whether couples have the trail all to themselves or share it with throngs of tourists, the loop delivers myriad, only-in-Oregon memories.

Hikers would do well to start with an ascent up Wahkeena Falls and into Wahkeena Canyon, where they’ll encounter a nice diversion in the fanning Fairy Falls. The trail continues deep into the forest, where hikers will feel miles away from one of the most popular tourist destinations in all of Oregon. The payoff comes soon thereafter, when the powerful Multnomah Falls comes into view and offers numerous, Instagram-worthy viewpoints.

Post-hike, couples could do worse than to snuggle up in the Multnomah Falls Lodge at the base of the falls. The lodge serves breakfast, lunch, and dinner, and will be offering a special Valentine’s Day menu on February 13-14.

For a Fun Tandem Bike Ride

The Smith and Bybee Wetlands offer a peaceful respite from the hustle and bustle of North Portland. Andy Price


North Portland’s mix of industry, residential neighborhoods, and pockets of nature might not exactly be considered a romantic setting. But the the North Portland Loop’s length, lack of elevation gain, and scenic beauty combine to make it a fun, leisurely excursion on a two-seater.

The loop starts in the quaint Kenton downtown hub before following the North Portland bluffs overlooking the Willamette River, passing the Smith and Bybee wetlands, and delivering views of innumerable iconic landmarks, including Mount Hood, downtown Portland, and Forest Park.

Take a break along the way for a pint or two at Occidental Brewing Company in the charming St. Johns neighborhood. The brewery prides itself on German-inspired beers—there’s nary an IPA on tap—and its wheaty Hefeweizen is a mainstay at Portland pubs.

For a Cozy, Post-Adventure Nosh

Backwoods Brewing Company serves up a variety of delicious beer in the Columbia River Gorge. Image Catalog


Backwoods Brewing Company, tucked away among the hills of the Columbia River Gorge, rewards diners with a solid beer selection (the Ridge Run Stout, with notes of coffee and chocolate, is a perfect complement to rainy February weekends) and mouth-watering pizzas. It’s a bit more casual than most Valentine’s Day dinners, but the restaurant’s ambiance—wood tables, an elegant wood bar, and fish-themed decor—reflects a regional sensibility that pairs well with a day outdoors. Not only that, but it’s a quick jaunt from dozens of popular hiking trails on both sides of the gorge.

While we’re talking food, take note: This will be your last Valentine’s Day season to enjoy Veritable Quandary in downtown Portland. The restaurant has dished up some of downtown’s finest fare for 45 years but will close this summer, paving the way for a new Multnomah County Courthouse. The restaurant is completely booked on Valentine’s Day, so we’d recommend a visit shortly before or soon after the holiday for a more relaxed, cozier vibe. (Maybe after a run along Tom McCall Waterfront Park?)

For Friendly, Flirty Competition

Disc golf at Dabney State Park is one adventurous, friendly, and fun Valentine’s Day idea. Rick Kim – U.S. Army


Playful competition can make for a fun date, and here in the Portland area, there are few better choices than disc golf at Dabney State Park.

The park, not far from Troutdale along the Sandy River, keeps things interesting with a course that’s equal parts scenic and tricky. Beautiful, tree-lined holes and open meadows quickly give way to challenging elevation changes, water hazards (in the form of creeks and ponds), and tough-to-spot baskets that will confound first-timers. But, then again, isn’t that part of the fun? (Friendly warning: The course can be quite muddy after rainfall, so plan on packing a pair of waterproof shoes or boots, just in case.)

Alternately, adventurers can get dirty on the My Muddy Valentine 5K Mud Run. The muddy race, happening on February 13 in Tualatin, features more than 20 challenging obstacles, bonfires to keep runners warm, one drink of choice (mimosa, cider, or beer), and more goodies. Couples and single runners alike can up the ante and aim for ribbons in various age groups, each of which will offer prizes for both singles and couples.

For a Sweet Solo Excursion

The hike along Coyote Wall offers impressive views of Mount Hood, across the Columbia River. Chad


Say you’re single, eschew the commercialism and hype of Valentine’s Day, and want to get far away from the corporate-mandated displays of affection.

We’ve got just the spot: The Coyote Wall to the Labyrinth hike (nearly 90 minutes out of Portland) offers solitude to go along with its stunning landscapes and scenery. And, given its location in the Columbia River Gorge, hikers can expect sunnier, milder weather than the dreary rain back in town.

The hike illustrates the natural variety that is one of the hallmarks of the Columbia River Gorge. Hikers will experience grassy fields, basalt outcroppings, majestic oak trees, rushing waterfalls, views of the gorge, and much more.

The hike gets busier in spring, when wildflowers line the landscape and mountain bike riders enjoy the wide-open scenery, so you may have the route all to yourself in the middle of winter. And if you’re single, that might be just the way you like it.

Featured image provided by Cordelia